Chiral solvating agents

Abstract

In an embodiment, a composition including a chiral solvating agent to resolve nuclear magnetic resonance signals of an enantiomer of at least one analyte, where the chiral solvating agent facilitates in the at least one analyte binding to a C2 face or a C3 face of the chiral solvating agent, and where the chiral solvating agent causes an upfield shift or a downfield shift in at least one nuclear magnetic resonance signals corresponding to a 1H, 19F{1H}, or 31P{1H} signal, and where the chiral solvating agent includes a cobalt cation. In another embodiment, a method that includes mixing a chiral solvating agent, including a cobalt cation, with at least one analyte to form a solution, obtaining nuclear magnetic resonance spectra of the solution, and identifying an enantiomer of the at least one analyte. In some embodiments, the method further includes determining enantiomeric purities of the at least one analyte.

What is claimed is: 
     
       1. A composition comprising:
 a chiral solvating agent to resolve nuclear magnetic resonance signals of an enantiomer of at least one analyte, wherein the chiral solvating agent facilitates in the at least one analyte binding to a C 2  face or a C 3  face of the chiral solvating agent; 
 wherein the chiral solvating agent causes an upfield shift or a downfield shift in at least one nuclear magnetic resonance signal corresponding to a  1 H,  19 F{ 1 H}, or  31 P{ 1 H} signal; 
 wherein the chiral solvating agent comprises a cobalt cation; 
 wherein the cobalt cation is selected from the group consisting of [Co((S,S)—NH 2 CHPhCHPhNH 2 ) 3 ] 3+ , [Co((R,R)—NH 2 CHPhCHPhNH 2 ) 3 ] 3+ , [Co((S,S)—NH 2 CHArCHArNH 2 ) 3 ] 3+ , [Co((R,R)—NH 2 CHArCHArNH 2 ) 3 ] 3+ , or combinations thereof; and 
 wherein Ar is a substituted or unsubstituted aryl group selected from the group consisting of a phenyl group, a naphthyl group, a furanyl group, or combinations thereof. 
 
     
     
       2. The composition of  claim 1 , wherein the cobalt cation is in the form of a salt comprising at least one lipophilic anion, lipophilic dianion, or lipophilic trianion. 
     
     
       3. The composition of  claim 1 , wherein the chiral solvating agent has a loading of between less than 1 mol % to 100 mol %. 
     
     
       4. The composition of  claim 1 , wherein the at least one analyte comprises a plurality of enantiomeric compounds. 
     
     
       5. A method comprising:
 mixing a chiral solvating agent, comprising a cobalt cation, with at least one analyte to form a solution; 
 obtaining nuclear magnetic resonance spectra of the solution; and 
 identifying an enantiomer of the at least one analyte; 
 wherein the cobalt cation is selected from the group consisting of [Co((S,S)—NH 3 CHPhCHPhNH 2 ) 3 ] 3+ , [Co((R,R)—NH 2 CHPhCHPhNH 2 ) 3 ] 3+ , [Co((S,S)—NH 2 CHArCHArNH 2 ) 3 ] 3+ , [Co((R,R)—NH 2 CHArCHArNH 2 ) 3 ] 3+ , or combinations thereof; and 
 wherein Ar is a substituted or unsubstituted aryl group selected from the group consisting of a phenyl group, a naphthyl group, a furanyl group, or combinations thereof. 
 
     
     
       6. The method of  claim 5 , further comprising determining enantiomeric purities of the at least one analyte. 
     
     
       7. The method of  claim 5 , wherein the cobalt cation is in the form of a salt comprising at least one lipophilic anion, lipophilic dianion, or lipophilic trianion. 
     
     
       8. The method of  claim 5 , wherein the chiral solvating agent has a loading between less than 1 mol % to 100 mol %. 
     
     
       9. The method of  claim 5 , wherein the at least one analyte comprises a plurality of enantiomeric compounds. 
     
     
       10. The method of  claim 5 , wherein the at least one analyte binds to a C 2  face or a C 3  face of the chiral solvating agent. 
     
     
       11. A composition comprising:
 a chiral solvating agent to resolve nuclear magnetic resonance signals of an enantiomer of at least one analyte, wherein the chiral solvating agent facilitates in the at least one analyte binding to a C 2  face or a C 3  face of the chiral solvating agent; 
 wherein the chiral solvating agent causes an upfield shift or a downfield shift in at least one nuclear magnetic resonance signal corresponding to a  1 H,  19 F{ 1 H}, or  31 P{ 1 H} signal; 
 wherein the chiral solvating agent comprises a cobalt cation; 
 wherein the cobalt cation is selected from the group consisting of [Co(en) 2 (NH 2 —CH 2 CH((CH 2 ) n N(CH 3 ) 2 )NH 2 )] 3+ , [Co(en) 2 (NH 2 CH 2 CH((CH 2 ) n N(R)(R′))NH 2 )] 3+ , or combinations thereof; and 
 wherein R and R′ are each selected from the group consisting of H, Ph, Bn, an alkyl group, an aryl group, Si(R 1 ) 2 (R 2 ), C(R 1 ) 2 (R 2 ), or combinations thereof; and 
 wherein R 1  and R 2  are each selected from the group consisting of H, Ph, Bn, an alkyl group, an aryl group, or combinations thereof. 
 
     
     
       12. A method comprising:
 mixing a chiral solvating agent, comprising a cobalt cation, with at least one analyte to form a solution; 
 obtaining nuclear magnetic resonance spectra of the solution; and 
 identifying an enantiomer of the at least one analyte; 
 wherein the cobalt cation is selected from the group consisting of [Co(en) 2 (NH 2 —CH 2 CH((CH 2 ) n N(CH 3 ) 2 )NH 2 )] 3+ , [Co(en) 2 (NH 2 CH 2 CH((CH 2 ) n N(R)(R′))NH 2 )] 3+ , or combinations thereof; and 
 wherein R and R′ are each selected from the group consisting of H, Ph, Bn, an alkyl group, an aryl group, Si(R 1 ) 2 (R 2 ), C(R 1 ) 2 (R 2 ), or combinations thereof; and 
 wherein R 1  and R 2  are each selected from the group consisting of H, Ph, Bn, an alkyl group, an aryl group, or combinations thereof.